Synthesis of pyridinium dinitrobenzyl sulfates and potassium (dinitrobenzyl beta-D-glucopyranosid)uronates.
Sulfates and glucuronides of 2,4-dinitrobenzyl alcohol 1a and 2,6-dinitrobenzyl alcohol 1b, which are major or putative metabolites of 2,4-dinitrotoluene (2,4-DNT) and 2,6-dinitrotoluene (2,6-DNT), were synthesized from 1a and 1b by reaction with pyridinium sulfonate and methyl (2,3,4-tri-O-acetyl-alpha-D-glucopyranosyl)uronate bromide 3, respectively, as their pyridinium salts (2a, 2b) and potassium salts (6a, 6b). These conjugates are important for the study of the carcinogenicity of 2,4-DNT and 2,6-DNT.
Mori
M
M
School of Health Sciences, Kyushu University, Fukuoka, Japan.
Dohrin
M
M
Sayama
M
M
Shoji
M
M
Inoue
M
M
Kozuka
H
H
D001592:Benzyl Alcohols / Q000737:chemistry; D002273:Carcinogens / Q000737:chemistry; D004136:Dinitrobenzenes / Q000737:chemistry; D005965:Glucuronates / Q000138:chemical synthesis; D011726:Pyridinium Compounds / Q000138:chemical synthesis*; D013431:Sulfates / Q000138:chemical synthesis; D014574:Uronic Acids / Q000138:chemical synthesis*
D001592:Benzyl Alcohols; D002273:Carcinogens; D004136:Dinitrobenzenes; D005965:Glucuronates; D011726:Pyridinium Compounds; D013431:Sulfates; D014574:Uronic Acids; C029332:2,4-dinitrobenzyl alcohol; C023514:2,6-dinitrotoluene